Cottage holiday rentals in Chincoteague

A cozy cottage exterior is presented with a light blue façade and a welcoming front porch. The entrance features a small overhang and steps leading to the front door, accompanied by neatly trimmed bushes and a well-maintained lawn under clear blue skies.

4.94 out of 5 average rating, 191 reviews

Maggie’s Cottage on Poplar - Our Happy Place!

Step back in time and enjoy the simplicity of this 2 bedroom, 1 bath vintage Chincoteague cottage located in the heart of town. Quaint, quiet and cozy - Maggie’s Cottage is the perfect retreat to slow down, relax, and enjoy an island get away... anytime of the year! Maggie’s Cottage is just right for a couples get away, girls trip, a solo retreat, or a small family vacation. Well stocked and comfortable- you will feel right at home. Walking distance to local dining, shopping and waterfront!🐴🦪🌅

A sandy beach borders calm waters, reflecting sunlight under a bright blue sky filled with clouds. Dark rocks and a grassy area play a role in the natural landscape, while distant structures along the shore suggest waterfront access.

4.92 out of 5 average rating, 224 reviews

Chesapeake Bay Beach Cottage

This cozy coastal cottage offers the ability to enjoy everything the Northern Neck has to offer including the reason we own it - Beach Days! No high rise hustle and bustle, just old school Northern Neck relaxation at the beautiful Chesapeake Bay. Unwind with books, games & toys or get out and do it all... Boating, (we have a brand new double boat ramp 1/4 ml from the house) Beach , Water Activities, History, Dining and more. Fully stocked kitchen & outdoor shower. We also have the fastest. WiFi.

4.95 out of 5 average rating, 254 reviews

The exterior of Westview Cottage is shown, featuring a well-maintained lawn with lush greenery. Floor-to-ceiling glass doors are visible, reflecting the surrounding landscape and allowing natural light into the cottage. Trees and shrubs frame the view, enhancing the serene atmosphere.

Cottage in Onancock

Eastern Shore Romantic Waterfront Getaway Upscale

A waterfront getaway at the newly renovated Westview Cottage on Onancock Creek just off the Chesapeake Bay. Wake up to beautiful water views through floor-to-ceiling glass doors. A private, peaceful escape in the country conveniently surrounded by fields and wildlife complete with a dock for crabbing and fishing (seasonal) 4 MI to Downtown Onancock & Restaurants 4.5 MI to Walmart 25 Mi to Camp Silver Beach 35 MI to Chincoteague Island 39 MI to Cape Charles >save listing to your wishlist<<

Adirondack chairs are arranged in a semicircle facing a stunning sunset over Chincoteague Bay. The sky reflects hues of orange and pink, while the calm waters mirror the colors above. A firepit is positioned nearby, surrounded by tall grasses.

4.96 out of 5 average rating, 157 reviews

Waterfront-CI Bay sunsets-Amazing views

Wide expansive waterfront view of Chincoteague bay-awesome sunsets! 5 waterview rooms. The narrow bit of land across 3446 Main St. belongs to our property w/chairs + a firepit + water access to launch kayaks (2) provided! An open plan-coastal rustic design. Front sitting room w/sofa + high-top table. A large upscale kitchen, two sofas in living room, 2 bdrms, & sleeping loft + a tiny office with a twin murphy bed. Large deck-table, sofa + grill. Family home, not ideal for more than 3 adults.

4.98 out of 5 average rating, 149 reviews

A charming cottage stands surrounded by lush grass, with a large tree providing shade in the foreground. The white exterior features a welcoming entrance with step access, flanked by neatly trimmed bushes and colorful potted plants. A serene open field extends beyond the cottage.

Cottage in Greenbush

Bell Farm Cottage LLC - quiet and peaceful

Cozy cottage located on a quiet backroad overlooking a wide open field & back deck provides warm & sunny space for relaxing or reading a book. The kitchen is fully equipped. BFC has a warm farm house feel w/ a touch of the beach. The bathroom has been updated to a more modern feel. Located only a few miles from both seaside and bayside boat ramps. A 7 minute drive to Onancock, Walmart, YMCA, shopping & many local shops for just the right souvenir. Wallops & Chincoteague are just a short drive.

The exterior of Ivy's Cottage showcases a charming gray shingle facade with a welcoming purple front door. A set of steps leads to a spacious porch, which is accompanied by white railings and decorative plants, enhancing the inviting entryway.

4.85 out of 5 average rating, 112 reviews

"3 Sisters" Ivy's Cottage-Lovely downtown cottage

Just a few miles from the Chincoteague National Wildlife Refuge & Assateague Beach. Ivy's Cottage offers a great in-town location that's close to shops, restaurants, waterfront park, & public fishing pier. This beautifully renovated, this Chincoteague Island Cottage Features: Lovely eat in kitchen, fully equipped w/ all amenities. Cozy living room w/ full sleeper sofa & recliner. Queen bedroom w/ adjacent full bathroom. Large front porch perfect for outdoor dining & park style charcoal grill!

4.95 out of 5 average rating, 140 reviews

A Victorian cottage sits on a private island, surrounded by a serene lake. The green roof contrasts with the pastel exterior, while a footbridge leads to the shore. Lush grass and scattered trees create a peaceful landscape, with distant water views enhancing the setting.

Cottage in Hacksneck

Pretty Byrd Cottage, a Victorian Bayfront Getaway!

Imagine getting away from it all by crossing a footbridge to a private island with a Victorian cottage on your own private 3-acre lake! This property is a unique oasis that combines today's modern conveniences with the charm of elegant decor. Enter the front door and be taken in by the surrounding water views, and enjoy charming verandas and a balcony that overlook the lake and gardens surrounding the cottage. Guests can also enjoy the use of a private beach, fishing, kayaks and a paddleboat!

4.94 out of 5 average rating, 177 reviews

A spacious deck offers breathtaking views of the water at sunset, with a stunning orange and pink sky. Four Adirondack chairs are arranged around a brown wicker coffee table, complemented by striped cushions. The serene water reflects the evening sky, creating a tranquil atmosphere.

Cottage in Onancock

A "True" Chesapeake Bay Waterfront Experience!

Get away from it all... The Thicket Point Fish Camp is a true Chesapeake Bay waterfront property and the perfect place to escape for the best of the Eastern Shore. Located just 5 miles from downtown Onancock, VA, and everyday conveniences, this property is one of a kind! This is the "Sunset House" expanded and completely renovated in May 2018, It is complemented by our "Bayside House" - also available on Airbnb. Be ready for the smell of the salt air and to enjoy million-dollar sunsets!

4.99 out of 5 average rating, 198 reviews

A charming cottage facade is framed by white columns and features a gabled roof. Two black rocking chairs, adorned with pillows, sit on a brick porch surrounded by colorful potted flowers. Lush greenery enhances the inviting atmosphere.

Cottage in Frankford

19th Century Cottage with Modern Amenities

Book your Hallmark Christmas stay today, fully decorated until the end of January with low rates!! Built from “clinker bricks” in 1941 to house poultry feed, this Airbnb is a dreamy place to slow down. This charming cottage near the beach & is surrounded by enchanted gardens. You will swoon over the carved marble bathtub and gorgeous living areas. Perfect for a romantic getaway, Hobbs and Rose Cottage is waiting to create a memorable experience for you! NEW for 2025, our mediation room!

A serene waterfront view captures a calm body of water reflecting a colorful sunset. Silhouettes of grass line the shore, while a long pier extends into the distance, adding depth to the tranquil scene.

4.95 out of 5 average rating, 178 reviews

Summer's Sea Shanty on Chincoteague Island

Summer's Sea Shanty is a delightful Chincoteague coastal cottage that’s perfect for couples, families, or small groups of friends. We've worked hard to make this the ideal modern day beach retreat. This home boasts screened in front and back porches, a fire pit, an open/functional floor plan. We're pet and kid friendly with luxury linens and rugs and dish ware... We're proud to be the best of the best on the island. We're centrally located and minutes from Assateague National Seashore.

A serene view of a cove with gentle waves lapping against a sandy shore. The calm water reflects the clear blue sky and nearby greenery. Footprints are visible in the sand, leading toward the water's edge.

4.91 out of 5 average rating, 212 reviews

"Dragonfly" Waterfront Cottage on Chesapeake Bay

Bayfront beach vacation? Kayak out to dolphins? Breathtaking sunrises & sunsets? Yes, please! Relaxation and fun await at 'Dragonfly', a gorgeous cottage right on the Chesapeake Bay with spectacular views from every room. Nestled on acres and acres of waterfront, this magical property has its own cove for all the swimming, kayaking, SUP boarding and fishing you can manage. If you love nature, bring your water shoes and sense of adventure and we will take care of the rest!

4.89 out of 5 average rating, 380 reviews

The cottage features a welcoming front porch with a flag gently waving. Lush greenery surrounds the entrance, complemented by a grassy lawn under a clear blue sky, creating an inviting approach to the home.

Cottage in White Stone

The Moore Cottage

The Moore Cottage is a rustic-chic, fisherman's cottage.The cottage is less than a mile from Windmill Point Marina, and five miles from the town of White Stone. You will enjoy the views of amazing wildlife, boaters, the beach, and breath-taking sunsets all while sitting on the back porch. The Cottage is nestled on a cove overlooking Little Bay and the mouth of Antipoison Creek. Come check out one of the Northern Neck's best kept secrets!

Popular amenities for cottage rentals in Chincoteague

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

The front exterior of the creek house is shown, featuring a welcoming porch with steps leading up. A colorful flag waves gently, and vibrant greenery surrounds the area, while a white railing offers a pleasant border. The house has a light beige facade complemented by green accents.

Cottage in Newark

4.89 out of 5 average rating, 54 reviews

Cropper Creek House

A view of an outdoor area featuring a waving American flag illuminated by soft string lights. The scene includes a backdrop of lush green grass and trees, with a serene canal reflecting the evening sky's colors.

Cottage in Bethany Beach

4.82 out of 5 average rating, 22 reviews

Bethany Beach Sea Colony Canalside Sleeps 7

5 out of 5 average rating, 81 reviews

Cottage in Woolford

Waterfront Cottage Near Cambridge w/Hot Tub

4.86 out of 5 average rating, 22 reviews

A serene waterfront property is displayed, featuring a two-story structure with a spacious deck overlooking the sandy beach. The outdoor area includes lounge chairs and a nearby kayaks, all framed by calm waters and lush greenery in the background.

Cottage in Scotland

Hays Beach House - Hot Tub - Private Beach

Cottage in Marion Station

An aerial view showcases a rustic-modern house surrounded by greenery. Red pathways lead to the entrance, and a wooden deck is visible with steps leading up to the front door. In the background, a private pool and shaded seating areas offer outdoor relaxation options.

4.77 out of 5 average rating, 48 reviews

Year Round Playground - Rare Rustic-Modern Getaway

4.89 out of 5 average rating, 54 reviews

The cottage exterior features a welcoming design with a red front door, surrounded by a gravel pathway and lush greenery. Large windows brighten the facade, while a porch with railings offers a relaxing space to enjoy nature.

Cottage in Selbyville

"Bayside" Coastal Cottage w/ Golf, Hot Tub + EV

A hot tub is positioned on a wooden deck, overlooking the shimmering waters of the Chesapeake Bay. Surrounding greenery includes tall grasses and trees, with the expansive view of the water framed by a clear blue sky.

4.89 out of 5 average rating, 231 reviews

Bay cottage 🏖on the beach. Stunning views🏝

Pet-friendly cottage rentals

4.84 out of 5 average rating, 192 reviews

The exterior of the cottage is framed by a covered porch featuring large screens, surrounded by trees and natural light. Two green Adirondack chairs and two dark wooden chairs are set on the ground, inviting relaxation in the outdoor space.

Cottage in Deltaville

The Little House at Waveland

4.9 out of 5 average rating, 109 reviews

A serene sunset is captured over calm waters, with hues of orange and gold reflecting on the surface. Silhouettes of trees frame the scene, while a dock extends into the bay, creating a tranquil coastal atmosphere.

Cottage in Painter

Cottage by the bay (private peaceful surroundings)

5 out of 5 average rating, 101 reviews

A spacious cottage exterior is framed by vibrant green landscaping and a well-maintained lawn. American flags are displayed prominently, and a covered porch offers access to the home's entrance. Surrounding trees provide a natural backdrop, enhancing the peaceful setting.

Cottage in Kilmarnock

Cottage on Prentice Creek, PA

4.97 out of 5 average rating, 33 reviews

A wooden deck is shown with a round table and four black mesh chairs, facing the calm waters of the Wicomico River. Lush greenery surrounds the area, with a dock visible in the background. The sky features soft clouds, enhancing the serene atmosphere.

Cottage in Princess Anne

Waterfront Cottage in Mt. Vernon

4.93 out of 5 average rating, 106 reviews

An aerial view captures the farmhouse situated along the banks of Henry's Creek, surrounded by lush greenery. A dock extends into the water, providing access for outdoor activities. The rural landscape and nearby road are visible, emphasizing the peaceful setting.

Cottage in Kilmarnock

Creeks End Farmhouse

Superhost

A charming cedar cottage is surrounded by lush greenery, featuring a green metal roof and a welcoming front porch. A white picket fence outlines the property, with gravel pathways leading up to the entrance. Mature trees provide a natural canopy, enhancing the peaceful setting.

Cottage in Delmar

4.88 out of 5 average rating, 103 reviews

The Good Vibe Cottage

4.97 out of 5 average rating, 107 reviews

A cottage is set within a private wooded yard, surrounded by lush greenery. The exterior features white siding and black shutters. A grassy area leads to a wooden porch with steps, while a seating area is visible in the garden, offering a peaceful retreat.

Cottage in Cambridge

Cambridge Cottage

4.93 out of 5 average rating, 153 reviews

The image captures a serene sunset over water, with a shared pier extending into the view. Silhouettes of individuals can be seen near the pier, while golden and orange hues blend with dark clouds in the sky, creating a tranquil and scenic atmosphere.

Cottage in Deal Island

Water View Cottage

Private cottage rentals

Superhost

Two wooden Adirondack chairs are positioned on a weathered dock, facing towards a calm waterway. A shaded structure is visible on the left, while boats are anchored in the distance against a backdrop of blue skies dotted with white clouds.

4.73 out of 5 average rating, 110 reviews

SNUG HARBOR waterfront cottage with a grand view!

4.98 out of 5 average rating, 63 reviews

The exterior of the cottage is displayed, featuring a welcoming front porch with seating. Lush greenery surrounds the home, and a gravel pathway leads to the entrance. Large windows allow natural light, and a decorative plant is positioned near the entrance.

Cottage in Ocean Pines

3-bedroom cottage in Ocean Pines

5 out of 5 average rating, 57 reviews

Cottage in Smith Island

IDLE HOUR 3 BR 1 1/2 B w/ golf cart rental

4.94 out of 5 average rating, 53 reviews

A wooden dock extends over calm waters, bordered by trees and natural landscaping. The clear blue sky reflects on the surface, while distant trees and a cabin can be seen along the shoreline, contributing to a serene outdoor setting.

Cottage in Kilmarnock

Restful river house with water & golf-course view

4.95 out of 5 average rating, 19 reviews

A beach area features a colorful striped umbrella providing shade over two blue folding chairs positioned on the sandy shore. Lush grass and a calm body of water create a serene environment, with wooden posts partially visible in the background.

Cottage in Diggs

Chesapeake Bay Beach Front cabin

4.89 out of 5 average rating, 45 reviews

A welcoming porch is featured, lined with wicker chairs adorned with colorful cushions. Potted flowers add a touch of nature, while the sunlight casts gentle shadows across the wooden flooring, creating an inviting atmosphere for relaxation.

Cottage in Gwynn

Sunset Haven

A serene view of the Chesapeake Bay stretches across the horizon, reflecting sunlight on the calm water. The beach area, featuring soft sand and gentle waves, leads up to trees dotting the shoreline. The cottage is nestled amidst the natural landscape.

4.91 out of 5 average rating, 55 reviews

Waterfront Bay Cottage w/ Your Own Private Beach